Title: Five Times Blair Bailed Chuck Out of Jail (and One Time She Didn't) [1/6]

Author: Diamondinsanity/karmawiccan

Rating: PG-13/T

Disclaimer: I own nothing.

Pairing: Chuck/Blair, Blair/Nate

Spoilers: None really.

Timeline: Pre-series—Sophomore year

Word Count: 2465

Summary: Five times Blair had to pick Chuck up from jail, and one time they both needed to be picked up from jail.

Author's Notes: This is what happens when I should be studying for my juvenile delinquency exam…

"I need you to get me from the 101st precinct." Chuck's voice greeted her without so much as a hello. "Oh. And could you bring me clothes?"

Blair blinked as the line when dead and immediately decided that she wasn't picking him up from a precinct. She didn't even know where the 101st precinct was. So despite the fact that she had decided not to pick him up, she googled it only to find that it was in Queens.

She was most definitely not going to Queens to pick up Chuck Bass. Like she would let anyone catch her going to Queens, and tipping off Gossip Girl. And yet she couldn't help but wonder what the hell he was doing in Queens that got him arrested.

Sighing she checked the time. It was two in the morning. Nope. There was no way that she was picking him up from a police station in Queens at two in the morning. And yet she stripped out of her nightdress and into a pair of jeans and a sweater.

"Nate's in the Hamptons." She reasoned out loud as she grabbed her purse. "He would want me to pick his best friend up from jail." Still even as she said that, she couldn't help but to wonder why he hadn't just called one of his many whores. Or Georgina. Georgina always loved seeing him down on his luck. He should have called Georgina.

Silently she snuck through the penthouse, fearing that the sound of the elevator would awake one of her parents and she would be caught trying to rescue Chuck Bass from Queens. When she didn't hear either parent come out of their room, she slid into the elevator, saying a quick prayer in hopes she would get out of this without anyone knowing she was going to Queens.

She made sure she didn't see anyone she knew before hailing a cab and heading to the Palace. Suddenly she found herself wondering again why she was doing this. He was only her boyfriend's best friend, and Chuck Bass; no one that important. And yet she couldn't help but to know that he would do the same thing for her. Not that she would ever get arrested in Queens of course. She, unlike Chuck, has taste. But bailing each other out of jams did seem to be their thing lately. She just couldn't figure out how it went from social destruction to jail.

Once the cab was at the Palace, she double checked for anyone who looked like they read Gossip Girl before dashing out of the cab. She stalked over to the concierge desk and bit her lip softly. A year or so ago she and Chuck had come up with an emergency phrase so she could get his spare key in order to sneak Drunk Nate home when Chuck was out on his 'house calls.' It had been a joke suggestion at the time. She hadn't actually believed that Chuck would want her to use that phrase to get his spare key. And yet he'd been only too eager to use it. Apparently he liked making her uncomfortable.

A part of her didn't think getting Chuck's clothes was worth getting the spare key that he wouldn't let her keep (he said that he didn't want her walking in on him with anyone, and that the key was to be kept at the front desk and only used to pick Nate up). But she did it any way. After all, this meant that she got to dress him. It had possibilities.

"Hi. I forgot my key to my boyfriend's suite. Room 1812." She said in her most convincing voice, knowing very well that claiming to be Chuck's girlfriend was not convincing to anyone who actually knew him. But that was the joke she got stuck with. If only she hadn't made the mistake of saying that dating Nate was like dating Chuck as well because they were almost always together and she always had to put up with both of their drunk asses.

The concierge looked at her, cocking an eyebrow. He knew very well whose suite that was. Who didn't know whose suite that was?

She was going to kill Chuck once he was out of jail. "I'm Blair." She shot him a 'don't you recognize me?' look. "Blair Waldorf." She added for clarification as she flashed him her id before pursing her lips together in fake suspicion. "I am the only woman on that list, aren't?"

The man blanched for a moment before nodding. "Of course you are, Miss Waldorf. I'm sorry." He handed her the spare key. "Did you want me to ring up there to make sure he's there?"

Blair looked at him. Obviously Chuck had trained the front desk well. When you had as many women as Chuck did, she figured it was something you needed to do. But she hadn't been making things up when she said she was the only woman on his 'list.' The only people on it were her, Nate and his father. Still, she couldn't help but to be impressed by the concierge's dedication to not cock blocking Chuck. "He's not up there obviously. Otherwise he would have given me his key." She smiled sweetly at him. "He asked me to pick up his scarf for him since we need it tonight."

Not waiting for the man's reaction, she stalked right up to the elevator, grateful to be hidden from the world. Like she wanted to be seen going to Chuck's suite at two in the morning. That just had scandal written all over it, and that was the last thing that she needed right now.

Once she was in his suite, she immediately went to his closet, making a face at the bright colors that assaulted her. Blair grinned as she survived her options. Oh the possibilities. At first she thought about making him wear something heinous, but quickly dismissed that option. After all, she was going to be seen with him, and she couldn't be seen with a bad dresser (even though some days he was pushing his luck with the clothes he chose).

Quickly she grabbed a pair of jeans, knowing that he would hate it. Chuck Bass did not wear jeans. Why he had a pair she did not know, but she was going to make him wear them. She also grabbed a sweater she knew he hated because Nate's mother had given it to him before dashing out of his suite and breaking the cardinal rule. She would not be returning his key this time.

She was in another cab and half way to Queens when she got the text message.

Spotted: B asking the concierge at the Palace for her boy friend's key. 1812, B? Last time we checked that was C's suite, and N was still in the Hamptons. Sleeping with the best friend, B? Classy.

"Does that bitch ever sleep?" Blair wondered out loud as she stared out the cab's window. That was it. She was going to kill Chuck.

When the cab arrived at the precinct, Blair all but stormed inside the building. She glanced around quickly to figure out her surroundings before marching up to the counter and throwing down Chuck's clothes. "I'm here to pick up my boyfriend." She all but ground out the words, surprising herself that she'd used the word 'boyfriend.' But then again it was an emergency…

The officer behind the counter eyed the clothes. "Let me guess. Charles Bass." He said dryly. "You here to get the girl, too? She's driving me insane. Can I see your ID?"

She frowned at him as she handed him the ID that said she was eighteen. "What girl? He wasn't with a Serena was he?" That was the last situation she wanted: both of her closest friends in jail. Not that it would be Serena since she was in Connecticut. But if it wasn't Serena, she was going to kill him. How dare he ask her to come to Queens of all places and pick up him and another woman? That was ridiculous. Especially if she was supposed to be playing his girlfriend.

"No." The officer frowned slightly as he handed her back her ID. "A Georgina."

Blair's face hardened. "She can stay behind bars." She lowered her voice slightly. "Where she belongs."

The officer laughed, figuring it just to be a lovers' spat. "I'll go get him."

She rolled her eyes as she leaned against the counter, waiting for him to come out. Of course he was with Georgina. It all made sense now. That didn't mean she liked it though.

"Bass!" She heard the officer's voice in the distance. "Your girlfriend's here. Time to go."

Blair leaned further over the counter as she attempted to hear what Chuck's reaction would be.


She sighed in relief that she hadn't overstepped any weird rule of theirs.

"No. Just Bass." The officer said firmly, and Georgina started swearing in the background.

"Sorry, G." Chuck's voice echoed out to her. "I guess B just doesn't like you. I wonder why."

Georgina's swearing began again.

Blair leaned further over the counter to attempt to hear more. In the process she leaned too far and the next thing she knew she was on the ground on the other side of the counter. "Ow…" She mumbled.

"Couldn't wait to see me, dear?"

She glanced up to see Chuck standing over her. Wait. Scratch that. Chuck standing over her wearing grey sweatpants. She blinked.

He rolled his eyes at her before grabbing her hands and pulling her to her feet.

Blair kept staring at him now noticing that he was wearing a grey t-shirt that said 'Police Department' on it. She blinked again. "Chuck…" She began slowly. "Where are your clothes?"

He ignored her and continued walking around the corner.

That was when she remembered that she was mad at him.

She stormed around the counter, and before he could reach his clothes began hitting him with her purse. "Georgina Sparks, Chuck? What the hell where you thinking?" She paused for a moment before continuing smacking him with her purse. "And how the hell did you end up in Queens."

Much to her surprise, he didn't try to fight her off. He just let her hit him with her purse as he studied her. "I was trying to get my clothes back." He stated.

Blair stared. "Why weren't your clothes on?" She suddenly froze. "Georgina?" She groaned. "Again? That girl is a walking STD. But then again so are you. I suppose its fitting." She hissed under her breath.

Chuck rolled his eyes. "We were playing strip poker. At least we were until she decided strip running was more enticing." He spotted the clothes on the counter. "Are these mine?" When he realized what she'd given him, he looked at her. "I'm not wearing that."

A sweet smile slipped onto her features. "Well, you're not going out in public in sweatpants. I won't allow it."

He grumbled for a moment before disappearing into the bathroom.

The officer looked at her. "So how long have you and Casanova been together?"

She pursed her lips together as she pretended to think about it. "Since kindergarten." That was how long ago Nate had stuck him with her. Dating Nate really had forced her to at least have to pretend to be Chuck's girlfriend when the situation called for it, and it was disgusting. But she did it was a smile on her face. Well… A fake one at least.

"So you allow your boyfriend to go streaking with your friends?" He asked her with a frown.

Blair faked a laugh. "Oh. Georgina and I aren't friends. And he's my ex-boyfriend after this."

"It was only strip poker."

Surprised to hear Chuck's voice, Blair spun around, and immediately began laughing at Chuck. There he stood barefoot wearing jeans and a brown turtle neck sweater. He looked ridiculous, and Blair suddenly felt like being woken up at two in the morning had been worth it.

"Can we go now?" Chuck all but whined when the officer started laughing as well.

Blair only smirked before sashaying out of the precinct, feeling Chuck following her like a puppy. She didn't say a word to him as she hailed a cab.

"You didn't bring me shoes, did you?"

She turned and raised an eyebrow at him. "I always knew that you would lose your pants without supervision." She replied before walking towards the cab. "And no."

He grumbled under his breath the entire way to the hotel.

"I could have left you there with Georgina."

He stopped grumbling just in time to get out of the cab, and then held his hand out expectantly to her. "Well, come on."

Blair stared at him. "I am not sleeping with you."

Chuck rolled his eyes. "No, but I'm also not going inside without an excuse for not having shoes on. So help me pretend to limp."

A laugh immediately escaped Blair's lips and she slid out of the cab. "Fine." She said with a shake of her head as she wrapped an arm around Chuck's waist and let him lean against her. "The things I do for you, Bass."

He snorted. "I make your life interesting, Waldorf."


The next morning Blair woke up, sprawled across Chuck's bed, a vague memory of being too tired to go home dancing through her head. She stretched, and glanced over to find Chuck sleeping on the couch. And people said he wasn't gentlemanly. You just had to threaten him with castration first.

Sighing when she saw that it was nearly noon, she fell back against his pillows before deciding to risk it and check Gossip Girl to see how bad the damage was.

Spotted: B and C returning to the Palace-

She exited from the message deciding suddenly that she didn't want to know any more. Didn't people have better things to do at four in the morning?

Sighing she checked for the inevitable message from Nate, expecting him to yell at her. She didn't have one. In fact, she didn't get a message from him all day. Nate didn't care that Gossip Girl thought she was dating his best friend.

She didn't know whether to be annoyed or pleased that he didn't believe Gossip Girl. Her boyfriend was hard to read ever since Serena went to boarding school.

That's when it dawned on her: some days it was easier to pretend to be Chuck's girlfriend than to actually be Nate's. Vaguely she wondered what that meant about her and Nate. And then she decided that if Chuck ever called her from jail again, she wouldn't pick him up. It just made things too complicated.